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Churchill Downs, home to The Kentucky Derby which is known for its rich traditions of fashionable hats, mint juleps, celebrity citings, and of course horse racing. The 2020 Kentucky Derby fashion has grown through the decades making it an event of style and statements. This year’s derby might have a slightly different look turning the attention from customized hats to masks. With the race date moving to September 5, 2020, fans will have a little more time to prepare their fancy new look.

This year, the employees and guests who plan to attend the Kentucky Derby will have a new set of guidelines to follow in response to the COVID-19 pandemic. One of the new guidelines will be the encouragement of facial masks while in the facility. So then it is only appropriate that the masks will match the much anticipated Kentucky Derby fashion. Could the customized mask, hat, dress ensemble of 2020 steal the show?

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The New Kentucky Derby Fashion Trend Of 2020

Kentucky Derby Fashion History

The spectacular Kentucky Derby fashion has never disappointed. Beginning in the 1920s through the 1950s, the fashion of the derby women did not fluctuate much. Women could be seen in a dress or suit completed with a matching jacket or petticoat. Let’s also not forget that hats and gloves followed suite to finish off any outfit. The real change in wardrobe came in the mid to late 1960s when modesty became a thing of the past, hemlines were raised and societal women were beginning to strut their stuff.

With the derby look beginning to change in the 60s, more women began taking pride in the loud colors and unique hat styles while still holding onto old fashion traditions. Little did we know that such a respectable event could have so much color, pattern, and print in one arena. As the decades progressed, the women’s suit eventually wore out of style with dresses still holding strong. The main event though continued to be the exotic, wild hats created by fashion artists months in advance. Did we ever think we would see a decade where hats at the Kentucky Derby were expected to be second in line to what could be the new Kentucky Derby fashion statement… facial masks.

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Kentucky Derby Fashion

Louisville Hat Makers

Some hat milliners in Louisville are switching to mask making to get through this year’s pandemic. When the Derby was postponed, businesses have been hit hard in Lousiville, especially those that rely heavily on profits from the Kentucky Derby fashion. Jenny Pfanenstiel, has created some extravagant hats for some pretty famous people including Oprah and Madonna. Pfanenstiel along with other Louisville milliners are still creating some hats and making masks to match. Clients are now asking not just for a mask for safety reasons, but now artsy masks to match outfits.

Another hat milliner, Christine A. Moore is a hat designer that is turning her creative hat-making energy into creating masks for a community in need. Derby-goers would have submitted special orders and shops would have been selling her unique items, but this year gave her a different plan. This year Moore’s creative mask designs are being donated for free. Moore notes that mask-making isn’t nearly half as lucrative as selling her unique hat designs but she is still designing and creating pieces of art, just in a slightly different fashion.

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The New Kentucky Derby Fashion Trend Of 2020

Virtual Kentucky Derby Parties

For some, a backyard Kentucky Derby fashion party is an annual tradition. Friends gather, get dressed up, drink mint julips, and bet on their favorite horse. This year, plan a virtual party and gather friends near and far. Hosting a virtual Kentucky Derby party can be a lot of fun and getting dressed up might just be a great way to get out of your comfy clothes and into a nice dress for a couple of hours. Here are some ideas for setting up your virtual gathering:

Decorations – The great thing about a virtual party is that you can decorate as much or as little as you would like since your screen can be set to one wall or location. The official flower for the race are roses so a nice centerpiece of these beautiful flowers would add a great touch to any table. A race-themed wall could also be a fun feature or using a virtual background (horse themed) from your video chatting platform is sure to get everyone in the racing mood.

Cocktail Hour – The Kentucky Derby is not complete without a mint julep. Hopefully, if you have these in-person parties annually you have a garden of mint just waiting to dive into its bourbon bath. Depending on how large your party is, it might be fun to send each guest a small Kentucky Derby cocktail drink kit so everyone can practice their mixology skills and toast to kick off the race.

Derby Fashion – You know you’re in a pandemic when “cozy at home” becomes a category when shopping online. Make this virtual party a celebration and one to remember by getting out of your comfort wear and putting on your best-dressed outfit. It could be fun to encourage a hat decorating competition where everyone designs a hat of choice and all virtual attendees vote on the most creative design. Or class it up a bit by voting on a best-dressed couple wearing their ideal Kentucky Derby fashion. Whatever you decide, getting out of your sweats for a few hours might make you feel human again.


The Kentucky Derby fashion has transformed throughout the decades and 2020 is no different. This year prepare for custom made hat designs and masks to match. Ensuring safety doesn’t mean that color, design, and style should look any different. The date of the derby may have changed but one thing is for sure, there will still be mint juleps flowing, a winning horse, and of course derby-goers sporting their brightest colored masks across all of Churchill Downs. May the best fashionista win!

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The New Kentucky Derby Fashion Trend Of 2020

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